Triethylamine → Benzofuran-5-yl(phenyl)methanone

HRID 2075192

反応式

HRID 2075192 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[OH:11])=[CH:9][C:4]=2[CH:3]=[CH:2]1.C(N(CC)CC)C.C(Cl)Cl.CS(C)=O>CS(C)=O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[O:11])=[CH:9][C:4]=2[CH:3]=[CH:2]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 21912085Dimethylsulfoxide-dichloromethaneHCID 58415371Benzofuran-5-yl(phenyl)methanol

生成物 1

HCID 58415352Benzofuran-5-yl(phenyl)methanone

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
0 °C

実験手順

To a solution of benzofuran-5-yl(phenyl)methanol (4.0 g, 18 mmol) and triethylamine (7.3 mL, 54 mmol) in 30 mL 1:1 DCM/DMSO under nitrogen at 0° C. was added a solution of SO3*py (8.5 g, 54 mmol) in 20 mL DMSO dropwise via addition funnel. The reaction was allowed to stir 5 h at 0° C. and was quenched by addition of water and 250 mL Et2O. The organic layer was washed with water, 1N HCl, 1N NaOH, brine, and was dried over sodium sulfate, filtered, and concentrated. The resulting solid benzofuran-5-yl(phenyl)methanone was used without further purification. MS (ESI) m/z: Calculated: 222.1; Observed: 223.0 (M++1).

後処理

  1. additiondropwise via addition funnel
  2. customwas quenched by addition of water and 250 mL Et2O
  3. washThe organic layer was washed with water, 1N HCl, 1N NaOH, brine
  4. dry with materialwas dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting solid benzofuran-5-yl(phenyl)methanone was used without further purification

出典と根拠

ORDレコード
ord-770de3bda5be496e98d3f55f52d5696b
出典データセット
uspto-grants-2011_04
特許番号
US07919519B2

関連ノート

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